EP0906281B1 - Verfahren zur reinigung von sterisch gehinderten 4-amino-piperidinen - Google Patents
Verfahren zur reinigung von sterisch gehinderten 4-amino-piperidinen Download PDFInfo
- Publication number
- EP0906281B1 EP0906281B1 EP97927086A EP97927086A EP0906281B1 EP 0906281 B1 EP0906281 B1 EP 0906281B1 EP 97927086 A EP97927086 A EP 97927086A EP 97927086 A EP97927086 A EP 97927086A EP 0906281 B1 EP0906281 B1 EP 0906281B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- piperidines
- tad
- distillation
- mbar
- von
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
Definitions
- Substances which are solid under normal conditions advantageously compounds MXH 4-m Y m , in which M is an alkali metal, NR 4 , where R is identical or different C 1 -C 4 alkyl groups, or an equivalent of an alkaline earth metal or an equivalent are generally used as reducing agents Zinc, preferably an alkali metal, in particular sodium or potassium, for example sodium, and X is aluminum or in particular boron, Y CN or preferably H and m is 1 or in particular 0.
- An example is sodium borohydride.
- (R a O) 2 TiBH 4 or (R a O) 3 TiBH 4 in which R a represents a C 1 -C 4 alkyl group, have also proven successful.
- reducing agent In addition to the colorless product thus obtained, one can additionally Add small amounts of reducing agent to ensure storage stability to increase.
- the reducing agents are usually the substances mentioned above. They are generally in quantities from 0.001 to 0.02% by weight. Usually amounts are sufficient of up to 200 ppm of reducing agent. In special cases 100, 50 or 10 ppm are also sufficient.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Removal Of Specific Substances (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Im allgemeinen können Hochsiedergehalte von unter 0,1 Gew.-% im Piperidin I noch toleriert werden. Besser sind jedoch Hochsiedergehalte von weniger als 0,01 Gew.-%. Der Wassergehalt ist unkritisch, üblicherweise wird er auf unter 1 Gew.-% eingestellt.
- 87,2 % Triacetondiamin (TAD)
- 9,9 % H2O
- 1,5 % Tiefsieder
- 1,4 % Mittelsieder.
Lagerzeit in Tagen | Farbzahl (unverdünnte Ware) | |
(A) ohne NaBH4-Zusatz | (B) Zusatz von 110 ppm NaBH4 | |
13 | 43 | 5 |
14 | 37 | 6 |
16 | 37 | 5 |
18 | 38 | 4 |
19 | 40 | 3 |
20 | 38 | 7 |
21 | 41 | 11 |
22 | 36 | 8 |
25 | 48 | 13 |
32 | 36 | 3 |
39 | 43 | 4 |
Lagerzeit in Tagen | Farbzahl (unverdünnte Ware): (nach DIN-ISO 6271) | ||
ohne NaBH4-Zusatz | 1000 ppm | 100 ppm | |
1 | 238 | 207 | 225 |
3 | 297 | 16 | 61 |
4 | 289 | 12 | 35 |
5 | 287 | 10 | 27 |
6 | 286 | 9 | 32 |
10 | 299 | 5 | 73 |
11 | 297 | 4 | 72 |
42 | 309 | 3 | 255 |
Claims (4)
- Verfahren zur Reinigung von rohen Piperidinen der Formel I in der R1 bis R4 C1- bis C6-Alkyl, R1 und R2 und/oder R3 und R4 gemeinsam eine CH2-Kette mit 2 bis 5 C-Atomen bedeuten, dadurch gekennzeichnet, daß man in einem ersten Schritt hochsiedende Substanzen und gegebenenfalls Wasser aus den rohen Piperidinen destillativ abtrennt, in einem zweiten Schritt 0,01 bis 5 Gew.-%, bezogen auf das Produkt des ersten Schrittes, eines Reduktionsmittels zusetzt und in einem dritten Schritt die Piperidine durch Destillation isoliert.
- Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß R1, R2, R3 und R4 C1- bis C3-Alkyl bedeuten.
- Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß das Reduktionsmittel eine Verbindung der Formel MXH4-mYm ist, in der M ein Alkalimetall, NR4, wobei R gleiche oder verschiedene C1-C4-Alkylgruppen bedeuten, oder ein Äquivalent eines Erdalkalimetalles oder ein Äquivalent Zink, X Bor oder Aluminium, Y H oder CN und m 0 oder 1 bedeuten.
- Verfahren nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß man den durch Destillation im dritten Schritt isolierten Piperidinen I 0,001 bis 0,02 Gew.-%, bezogen auf die Piperidine, eines Reduktionsmittels zusetzt.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19622269 | 1996-06-03 | ||
DE19622269A DE19622269A1 (de) | 1996-06-03 | 1996-06-03 | Verfahren zur Reinigung von sterisch gehinderten 4-Aminopiperidinen |
PCT/EP1997/002822 WO1997046529A1 (de) | 1996-06-03 | 1997-05-30 | Verfahren zur reinigung von sterisch gehinderten 4-amino-piperidinen |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0906281A1 EP0906281A1 (de) | 1999-04-07 |
EP0906281B1 true EP0906281B1 (de) | 2001-11-28 |
Family
ID=7796031
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97927086A Expired - Lifetime EP0906281B1 (de) | 1996-06-03 | 1997-05-30 | Verfahren zur reinigung von sterisch gehinderten 4-amino-piperidinen |
Country Status (21)
Country | Link |
---|---|
US (1) | US6011157A (de) |
EP (1) | EP0906281B1 (de) |
JP (1) | JP2000511551A (de) |
CN (1) | CN1165524C (de) |
AT (1) | ATE209632T1 (de) |
AU (1) | AU716280B2 (de) |
BR (1) | BR9709470A (de) |
CA (1) | CA2257095C (de) |
CO (1) | CO4790110A1 (de) |
CZ (1) | CZ290805B6 (de) |
DE (2) | DE19622269A1 (de) |
EA (1) | EA001160B1 (de) |
ES (1) | ES2169397T3 (de) |
HU (1) | HUP0001750A3 (de) |
ID (1) | ID16996A (de) |
MY (1) | MY121277A (de) |
NZ (1) | NZ332160A (de) |
PL (1) | PL185707B1 (de) |
PT (1) | PT906281E (de) |
UA (1) | UA48229C2 (de) |
WO (1) | WO1997046529A1 (de) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19743433C1 (de) * | 1997-10-01 | 1999-04-22 | Basf Ag | Verfahren zur Reinigung von 4-Amino-piperidinen |
DE19912031A1 (de) | 1999-03-17 | 2000-09-21 | Basf Ag | Verwendung von quervernetztem Polyvinylpyrrolidon zur Erhöhung der Zerfallgeschwindigkeit von kompakten teilchenförmigen Wasch- und Reinigungsmitteln |
DE102008040045A1 (de) | 2008-02-01 | 2009-08-06 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
EP2085384A1 (de) | 2008-02-01 | 2009-08-05 | Evonik Degussa GmbH | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
CN116917272A (zh) | 2021-03-05 | 2023-10-20 | 巴斯夫欧洲公司 | 制备n,n'-二(2,2,6,6-四甲基哌啶-4-基)-1,6-己二胺的方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL266799A (de) * | 1961-07-07 | |||
US3159276A (en) * | 1963-05-03 | 1964-12-01 | Allied Chem | Ethanolamines |
US3222310A (en) * | 1963-11-20 | 1965-12-07 | Metal Hydrides Inc | Method for inhibiting color formation in amines |
JPS5522465B2 (de) * | 1973-01-24 | 1980-06-17 | ||
DE3003843A1 (de) * | 1980-02-02 | 1981-08-13 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von 4-amino-2,2,6,6-tetramethylpiperidin |
ES2067106T3 (es) * | 1990-09-24 | 1995-03-16 | Atochem North America | Purificacion y decoloracion de alquil-alcanolaminas de intenso color. |
US5208377A (en) * | 1990-09-24 | 1993-05-04 | Elf Atochem North America, Inc. | Purification and decolorization of off-color alkyl alkanolamines |
RU1811527C (ru) * | 1991-02-20 | 1993-04-23 | Научно-исследовательский институт химикатов для полимерных материалов | Способ выделени высокочистого 2,2,6,6-тетраметил-4-аминопиперидина |
-
1996
- 1996-06-03 DE DE19622269A patent/DE19622269A1/de not_active Withdrawn
-
1997
- 1997-05-30 BR BR9709470A patent/BR9709470A/pt not_active IP Right Cessation
- 1997-05-30 DE DE59705561T patent/DE59705561D1/de not_active Expired - Fee Related
- 1997-05-30 EP EP97927086A patent/EP0906281B1/de not_active Expired - Lifetime
- 1997-05-30 EA EA199801064A patent/EA001160B1/ru not_active IP Right Cessation
- 1997-05-30 CO CO97030212A patent/CO4790110A1/es unknown
- 1997-05-30 AU AU31700/97A patent/AU716280B2/en not_active Ceased
- 1997-05-30 NZ NZ332160A patent/NZ332160A/en unknown
- 1997-05-30 CZ CZ19983917A patent/CZ290805B6/cs not_active IP Right Cessation
- 1997-05-30 HU HU0001750A patent/HUP0001750A3/hu unknown
- 1997-05-30 CA CA002257095A patent/CA2257095C/en not_active Expired - Fee Related
- 1997-05-30 AT AT97927086T patent/ATE209632T1/de not_active IP Right Cessation
- 1997-05-30 CN CNB971942145A patent/CN1165524C/zh not_active Expired - Fee Related
- 1997-05-30 ES ES97927086T patent/ES2169397T3/es not_active Expired - Lifetime
- 1997-05-30 US US09/180,626 patent/US6011157A/en not_active Expired - Fee Related
- 1997-05-30 PL PL97330278A patent/PL185707B1/pl unknown
- 1997-05-30 PT PT97927086T patent/PT906281E/pt unknown
- 1997-05-30 UA UA98126948A patent/UA48229C2/uk unknown
- 1997-05-30 WO PCT/EP1997/002822 patent/WO1997046529A1/de active IP Right Grant
- 1997-05-30 JP JP10500210A patent/JP2000511551A/ja not_active Withdrawn
- 1997-05-31 MY MYPI97002410A patent/MY121277A/en unknown
- 1997-06-03 ID IDP971893A patent/ID16996A/id unknown
Also Published As
Publication number | Publication date |
---|---|
PL330278A1 (en) | 1999-05-10 |
EA001160B1 (ru) | 2000-10-30 |
AU716280B2 (en) | 2000-02-24 |
DE59705561D1 (de) | 2002-01-10 |
EA199801064A1 (ru) | 1999-06-24 |
CN1216979A (zh) | 1999-05-19 |
CA2257095A1 (en) | 1997-12-11 |
ATE209632T1 (de) | 2001-12-15 |
AU3170097A (en) | 1998-01-05 |
PL185707B1 (pl) | 2003-07-31 |
NZ332160A (en) | 1999-09-29 |
PT906281E (pt) | 2002-05-31 |
CO4790110A1 (es) | 1999-05-31 |
BR9709470A (pt) | 1999-08-10 |
MY121277A (en) | 2006-01-28 |
CA2257095C (en) | 2005-02-01 |
JP2000511551A (ja) | 2000-09-05 |
UA48229C2 (uk) | 2002-08-15 |
EP0906281A1 (de) | 1999-04-07 |
HUP0001750A2 (hu) | 2000-10-28 |
DE19622269A1 (de) | 1997-12-04 |
CN1165524C (zh) | 2004-09-08 |
CZ391798A3 (cs) | 1999-03-17 |
HUP0001750A3 (en) | 2003-07-28 |
US6011157A (en) | 2000-01-04 |
WO1997046529A1 (de) | 1997-12-11 |
ES2169397T3 (es) | 2002-07-01 |
CZ290805B6 (cs) | 2002-10-16 |
ID16996A (id) | 1997-11-27 |
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